Hydrazine hydrate (1:1) → tert-butyl N-((4-hydroxypiperidin-4-yl)methyl)carbamate

HRID 2407750Notes

Reaction equation

HRID 2407750 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.O.NN>C(O)C.[C].[Pd]>[OH:14][C:11]1([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11759029Tert-butyl (1-benzyl-4-hydroxy-4-piperidinyl)methylcarbamate

Product 1

HCID 10868112tert-butyl N-((4-hydroxypiperidin-4-yl)methyl)carbamateYield 104.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution the compound prepared in Example 250 (0.68 g) in ethanol (11 mL) was treated with hydrazine monohydrate (0.208 mL), followed by 10% palladium-carbon (0.238 g). The mixture was refluxed for 18 hours. After allowing mixture to cool to room temperature, the catalyst was filtered off and washed with methanol. The filtrate was evaporated in vacuo to obtain the title compound (0.510 g) having the following physical data.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. filtrationthe catalyst was filtered off
  3. washwashed with methanol
  4. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-8f12deb0e1e14d4a96c3a5e6bbe66b19
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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